EP0000528B1 - Neue organische Phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematozide - Google Patents

Neue organische Phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematozide Download PDF

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Publication number
EP0000528B1
EP0000528B1 EP78100412A EP78100412A EP0000528B1 EP 0000528 B1 EP0000528 B1 EP 0000528B1 EP 78100412 A EP78100412 A EP 78100412A EP 78100412 A EP78100412 A EP 78100412A EP 0000528 B1 EP0000528 B1 EP 0000528B1
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EP
European Patent Office
Prior art keywords
spp
general formula
chloride
preparation
stated above
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP78100412A
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German (de)
English (en)
French (fr)
Other versions
EP0000528A1 (de
Inventor
Junichi Saito
Akio Kudamatsu
Toyohiko Kume
Shinichi Tsuboi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience KK
Original Assignee
Nihon Tokushu Noyaku Seizo KK
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Publication date
Application filed by Nihon Tokushu Noyaku Seizo KK filed Critical Nihon Tokushu Noyaku Seizo KK
Publication of EP0000528A1 publication Critical patent/EP0000528A1/de
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Publication of EP0000528B1 publication Critical patent/EP0000528B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention relates to new organic phosphoric acid esters, a process for their preparation and their use as insecticides, acaricides and nematocides.
  • the compounds of formula (I) have been found to have excellent insecticidal, acaricidal and nematocidal activity.
  • R 1 is preferably alkyl with 1-3 C atoms (in particular methyl, ethyl or n-propyl), R 2 alkyl with 3 or 4 C atoms (in particular n-propyl, n-butyl, sec-butyl or isobutyl) or alkoxyalkyl with 3-6 C atoms (in particular 2- (C 1 -C 4 -alkoxy) ethyl such as methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl or n-butoxyethyl),
  • X denotes hydrogen, trihalomethyl (in particular trichloromethyl or trifluoromethyl) or alkoxy with 1-4 carbon atoms (especially ethoxy) and Y fluorine or chlorine.
  • Examples of the thiophosphoryl halides of the general formula (II) suitable as starting compounds in process variant (a) are 0-methyl-S-n-propylphosphorus chloride thioate, O-ethyl-S-n-propylphosphorus chloride thioate, O, S, - di-n-propylphosphorus chloride thioate , O - ethyl - S - n - butylphosphoric chloride thioate, 0 - ethyl - S - isobutylphosphoric chloride thioate, O - ethyl - S - sec.butylphosphoric chloride thioate, 0 - ethyl - S - methoxyethylphosphoric chloride thioate, 0 - ethyl - S - ethoxychlorothioate - n - propoxyethylphosphoric chloride thioate
  • alcohols and alcoholates of the general formula (111) suitable as starting materials in process variant (a) are 2,2,2 - trifluoroethanol, 2,2,2 - trichloroethanol, 1,1,1,3,3,3 - hexafluoro - 2-propanol, 1,1,1,3,3,3-hexachloro-2-propanol and 1-ethoxy-2,2,2-trifluoroethanol as well as the sodium or potassium salts of these alcohols.
  • thiophosphoryl halides of the general formula (IV) as starting compounds in process variant (b) are 0 - 2,2,2 - trifluoroethyl - S - n - propylphosphorus chloride thioate, 0 - 2,2,2 - trichloroethyl - S - n - propylphosphorus chloride thioate , O - 1,1,1,3,3,3 - hexafluoro - 2 - propyl - S - n - propyl phosphorus chloride thioate, 0 - 1,1,1,3,3,3 - hexachloro - 2 - propyl - S - n - propyl phosphorus chloride thioate, 0 - 2,2,2 - trifluoroethyl - S - n - butyl phosphorus chloride thioate, 0 - 2,2,2 - trichloro
  • alcohols and alcoholates of the general formula (V) which can be used as starting compounds in process variant (b) are methanol, ethanol and n-propanol and the sodium or potassium salts of these alcohols.
  • reaction can be represented by the following scheme:
  • Examples of phosphites of the general formula (VI) which are suitable in process variant (c) are 0 - methyl - 0 - 2,2,2 - trifluoroethylphosphite, 0 - methyl - 0 - 2,2,2 - trichloroethylphosphite, 0 - ethyl - 0 - 1,1,1,3,3,3 - hexafluoro - 2 - propylphosphite, 0 - ethyl - O - 1,1,1,3,3,3 - hexachlor - 2 - propylphosphite, 0 - ethyl - 0 - 1 - ethoxy - 2,2,2 - trifluoroethyl phosphite, O - n - propyl - 0 2,2,2 - trifluoroethyl phosphite, O -
  • sulfenyl halides of the general formula (VII) which are suitable as starting compounds in process variant (c) are 1-propanesulfenyl chloride, 1-butanesulfenyl chloride, isobutanesulfenyl chloride, 2-butanesulfenyl chloride, methoxyethanesulfenyl chloride, ethoxyethanesulfenyl chloride, n-propoxyethane and isopropyl chloride and n-isophenyl chloride, n-propenyl chloride and n-propenyl chloride the corresponding bromine salts called.
  • Each of the sulfenyl chlorides or bromides can easily be prepared by a conventional method which consists in reacting the corresponding disulfide with chlorine, bromine, sulfuryl chloride or sulfuryl bromide.
  • reaction can be represented by the following scheme:
  • the reaction according to variants (a), (b) and (c) of the process according to the invention can be carried out in the presence of an acid binder.
  • suitable acid binders are the hydroxides, carbonates, bicarbonates and alcoholates of the alkali metals and tertiary amines such as e.g. Triethylamine, diethylaniline or pyridine.
  • the end product can also be obtained with a good yield and high degree of purity if one works without an acid binder and instead thiophosphoryl halide of the formula (11) or (IV) with an alkali metal alcoholate of the formula (111) or (V) implements.
  • Process variants (a), (b) and (c) according to the invention are preferably carried out using a solvent or diluent.
  • solvents or diluents are water and inert organic solvents such as aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated) such as e.g.
  • Variants (a), (b) and (c) of the process according to the invention can be carried out within a wide temperature range.
  • the process is carried out at temperatures from -20 ° C to the boiling point of the mixture, preferably at 0-100 ° C.
  • the reaction is expediently carried out at atmospheric pressure, but it can also be carried out at elevated or reduced pressure.
  • the compounds according to the invention have excellent insecticidal, acaricidal and nematocidal activity. They can therefore be used to control plant pests and those pests which occur in the hygiene sector and in the supply or material protection sector and combine low phytotoxicity with good activity against stinging and biting insects and mites.
  • the compounds according to the invention can be used with great success as pesticides in the fields of crop protection, the hygiene sector and the protection of stored products.
  • the compounds according to the invention can also be used in the field of veterinary medicine, since they are effective against animal parasites, in particular ectoparasites such as e.g. parasitic fly larvae are effective.
  • Plant parasites among the nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp ..
  • the active ingredients can be in the usual formulations such as e.g. Solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed treatment powders, natural and synthetic materials impregnated with active ingredient, very fine capsules in polymer substances, seed coating compositions and Formulations intended for use in fumigation equipment such as: Fumigation cartridges, canisters and snakes as well as in ULV cold mist. and warm fog formulations are transferred.
  • fumigation equipment such as: Fumigation cartridges, canisters and snakes as well as in ULV cold mist. and warm fog formulations are transferred.
  • the formulations can be prepared by known methods, i.e. e.g. by mixing the active ingredients with extenders, i.e. liquid or liquefied, gaseous or solid diluents or carriers, optionally using surfactants, i.e. Emulsifiers and / or dispersants and / or foaming agents are produced. If water is used as an extender, organic solvents can e.g. can also be used as auxiliary solvents.
  • extenders i.e. liquid or liquefied, gaseous or solid diluents or carriers
  • surfactants i.e. Emulsifiers and / or dispersants and / or foaming agents are produced.
  • organic solvents can e.g. can also be used as auxiliary solvents.
  • aromatic hydrocarbons such as e.g. Xylene, toluene or alkylnaphthatine, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic or alicyclic hydrocarbons such as e.g. Cyclohexane or paraffins such as Petroleum fractions, alcohols such as e.g. Butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone or strongly polar solvents such as e.g. Dimethylformamide and dimethyl sulfoxide and water are suitable.
  • aromatic hydrocarbons such as e.g. Xylene, toluene or alkylnaphthatine
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene
  • Liquefied, gaseous diluents or carriers are to be understood as liquids which are gaseous at normal temperatures and pressure, e.g. Blowing agents for aerosols, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Ground solid minerals such as e.g. Kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly disperse silica, alumina and silicates.
  • Crushed and broken natural rocks such as e.g. Calcite, marble, pumice, sepiolite and dolomite, synthetic granules from inorganic and organic flours and the granules from organic materials such as Sawdust or sawdust, coconut shells, corn cobs and tobacco stems can be used.
  • nonionic or anionic emulsifiers such as e.g. Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysis products are used.
  • Suitable dispersants are e.g. Lignin sulfite liquors and methyl cellulose.
  • Adhesives such as e.g. Carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices such as Gum arabic, polyvinyl alcohol and polyvinyl acetate can be used.
  • Colorants such as inorganic pigments, e.g. Iron oxide, titanium oxide and Prussian blue and organic dyes such as Alizarin dyes, azo dyes or metal phthalocyanine dyes and trace nutrients such as the salt of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide and Prussian blue
  • organic dyes such as Alizarin dyes, azo dyes or metal phthalocyanine dyes and trace nutrients such as the salt of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the active substances according to the invention can be mixed in the formulations with other active substances such as e.g. Fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth regulators, plant nutrients and soil conditioners are used.
  • active substances such as e.g. Fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth regulators, plant nutrients and soil conditioners are used.
  • the formulations generally contain 0.1-95% by weight, preferably 0.5-90% by weight, of active ingredient.
  • the active compounds according to the invention can be used in the form of commercially available formulations or preparations prepared from these formulations.
  • the active substance content of the commercially available formulations can vary within a wide range.
  • the active substance concentration in the formulations used can be 0.0001-20% by weight, preferably 0.005-10% by weight of active substance.
  • the active ingredients can be used according to conventional methods suitable for the form of use in question.
  • the present invention also relates to an insecticidal, acaricidal or nematicidal composition which, as an active ingredient, mixes a compound according to the invention and contains a solid or liquefied, gaseous diluent or carrier or mixed with a liquid diluent or carrier containing a surface-active agent.
  • the invention also relates to a method for controlling insects, acarids or nematodes, which consists in the insects, acarids or nematodes or in their habitat being a compound according to the invention alone or in the form of a composition which, as an active ingredient, mixes a compound according to the invention with a Contains diluent or carrier is applied.
  • crops are obtained on agricultural products which are protected from damage by insects, acarids or nematodes by being drawn in areas to which a compound according to the invention alone or mixed with immediately before and / or during the growth of the plants a diluent or carrier is applied.
  • insecticidal, acaricidal and nematocidal activity of the compounds according to the invention can be seen from the bioassay examples below.
  • the compounds according to the invention are each designated by the number (in parentheses) of the corresponding preparation example, which is mentioned later in the description.
  • Sweet potato leaves were immersed in an aqueous formulation containing a predetermined amount of active ingredient.
  • the leaves are air dried and then placed in a 9 cm diameter petri dish. 10 larvae of the Spodoptere litura in the third stage of development are then placed in the Petri dish. The shell is kept in a climatic chamber at 28 ° C, after 24 hours the number of dead larvae is determined and the mortality rate is calculated. The results are shown in Table A.
  • a filter paper will. spread in a Petri dish 9 cm in diameter. Then 1 ml of an aqueous formulation, which was prepared according to Example A and has a predetermined active ingredient concentration, is introduced into the dish. 20 copies of the Callosobruchus chinensis are placed in the Petri dish and the dish is kept in a climatic chamber at 28 ° C for 24 hours. After this period, the kill rate is determined.
  • Rice plants about 10 cm high are planted in pots with a diameter of 12 cm.
  • An aqueous preparation which contains a predetermined concentration of active ingredient in the formulation prepared according to Example A is applied to the rice plants in amounts of 10 ml per pot. After the applied preparation has dried, wire mesh cages, each 7 cm in diameter and 14 cm in height, are placed over the pots, and 30 female adults of Nephotettix cincticeps, which is resistant to organophosphorus preparations, are used in each cage. The pots are then placed in a climatic chamber. After 24 hours, the number of dead insects was determined and the kill rate calculated. The results are shown in Table C.
  • a filter paper was placed in a Petri dish with a diameter of 9 cm and impregnated with 1 ml of an aqueous preparation which was produced according to Example A and had a predetermined active substance concentration. Then 10 female adults of the Musca domestica resistant to organophosphorus preparations were introduced into the dish. The dish was kept in a climatic chamber at 28 ° C for 24 hours, after which time the number of dead flies was determined and the kill rate calculated. The results are shown in Table D.
  • a filter paper was placed in a Petri dish with a diameter of 9 cm and impregnated with 1 ml of an aqueous preparation which had been prepared according to Example A and had a predetermined active ingredient concentration. 10 adults of the Blatella germanica were placed in the bowl, which was kept in a climatic chamber at 28 ° C for 24 hours, after which the number of dead insects was determined and the kill rate calculated. The results are shown in Table G.
  • An active ingredient preparation was prepared by pulverizing and mixing 2 parts by weight of active ingredient and 98 parts of talc.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100412A 1977-07-25 1978-07-17 Neue organische Phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematozide Expired EP0000528B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP88352/77 1977-07-25
JP52088352A JPS6021159B2 (ja) 1977-07-25 1977-07-25 有機リン酸エステル系化合物、該化合物の製造方法および該化合物を有効成分として含有する殺虫、殺ダニおよび殺センチユウ剤

Publications (2)

Publication Number Publication Date
EP0000528A1 EP0000528A1 (de) 1979-02-07
EP0000528B1 true EP0000528B1 (de) 1980-07-23

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EP78100412A Expired EP0000528B1 (de) 1977-07-25 1978-07-17 Neue organische Phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematozide

Country Status (23)

Country Link
US (1) US4189476A (tr)
EP (1) EP0000528B1 (tr)
JP (1) JPS6021159B2 (tr)
AR (1) AR220719A1 (tr)
AT (1) AT360276B (tr)
AU (1) AU517310B2 (tr)
BR (1) BR7803517A (tr)
CA (1) CA1110650A (tr)
CS (1) CS199738B2 (tr)
DD (1) DD138878A5 (tr)
DE (1) DE2860061D1 (tr)
DK (1) DK328078A (tr)
EG (1) EG13377A (tr)
ES (3) ES471989A1 (tr)
HU (1) HU182737B (tr)
IL (1) IL55198A (tr)
IT (1) IT1099576B (tr)
OA (1) OA06034A (tr)
PL (3) PL119038B1 (tr)
PT (1) PT68318A (tr)
SU (1) SU786850A3 (tr)
TR (1) TR19961A (tr)
ZA (1) ZA784182B (tr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5788414A (en) * 1980-11-21 1982-06-02 Seiko Epson Corp Alignment device
US4673664A (en) * 1985-10-07 1987-06-16 American Cyanamid Company Shape for extruded catalyst support particles and catalysts
DE3910662A1 (de) * 1989-04-03 1990-10-04 Bayer Ag Thiophosphorsaeure-fluoralkylester
DE4110972A1 (de) * 1991-04-05 1992-10-08 Bayer Ag O-(2-fluoralkyl)-s-alkyl-(di)thiophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung und ihreverwendung als schaedlingsbekaempfungsmittel
US6620362B1 (en) * 2002-06-14 2003-09-16 Nan Ya Plastics Corporation Method of manufacturing polyester fiber having improved light fastness

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3184377A (en) * 1961-12-12 1965-05-18 Chemagro Corp Method of killing nematodes with thiophosphates
DD107581A1 (tr) * 1973-05-02 1974-08-12
JPS6046137B2 (ja) * 1976-07-27 1985-10-14 三菱油化株式会社 熱可塑性樹脂組成物

Also Published As

Publication number Publication date
BR7803517A (pt) 1979-03-20
CS199738B2 (en) 1980-07-31
IL55198A0 (en) 1978-09-29
DE2860061D1 (en) 1980-11-13
PL208574A1 (tr) 1980-01-02
CA1110650A (en) 1981-10-13
DD138878A5 (de) 1979-11-28
IT1099576B (it) 1985-09-18
JPS5424829A (en) 1979-02-24
TR19961A (tr) 1980-05-16
JPS6021159B2 (ja) 1985-05-25
ZA784182B (en) 1979-07-25
IL55198A (en) 1982-12-31
EP0000528A1 (de) 1979-02-07
HU182737B (en) 1984-03-28
PL114565B1 (en) 1981-02-28
IT7825985A0 (it) 1978-07-21
PL114583B1 (en) 1981-02-28
ES471989A1 (es) 1979-10-01
ES479025A1 (es) 1979-07-01
DK328078A (da) 1979-01-26
AU517310B2 (en) 1981-07-23
OA06034A (fr) 1981-06-30
PT68318A (de) 1978-08-01
AU3828578A (en) 1980-01-31
EG13377A (en) 1982-09-30
ATA540178A (de) 1980-05-15
PL119038B1 (en) 1981-11-30
SU786850A3 (ru) 1980-12-07
AR220719A1 (es) 1980-11-28
AT360276B (de) 1980-12-29
ES479024A1 (es) 1979-07-01
US4189476A (en) 1980-02-19

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